


For the Weekend

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Bondage, Bottom Dean, Client Castiel, Dildos, Dirty Talk, Fingering, M/M, Name Calling, Older Castiel, Orgasm Denial, Painplay, Prostitute Dean, Prostitution, Rough Sex, Sex Toys, Spanking, Top Castiel, Twink Dean, cockcage, paid sex, rough castiel, spreader bar
Language: English
Status: Completed
Published: 2016-08-16
Updated: 2016-08-16
Packaged: 2018-08-09 02:33:43
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,413
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7783390
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: <blockquote class="userstuff">
              <p>Castiel purchases Dean, a high class prostitute, for a long weekend where he can do all of the things his regular lovers won't let him do.</p>
            </blockquote>





	For the Weekend

Castiel stared down at the naked slope of Dean’s back, the way he’d positioned the prostitute to put his pert ass on display, before mourning the fact that he was unable to leave any permanent marks on that freckled skin.

He might not be able to mark Dean but he didn’t have to deal with condoms for the whole weekend and it was worth it. He’d had to show he was clean before Dean would agree to fuck without a condom but once the man had seen the papers and showed his own Castiel was given the green light.

It was fortunate for him that there were only a few rules he had to keep in mind but other than that he could do as he wanted to the pretty prostitute tied up in front of him for the weekend. Almost every single thing he couldn’t do with his typical partners he planned on doing to Dean.

The money would be more than worth it.

“Feel free to scream, moan, beg, wail or whatever sound finds itself falling from those pretty cock-sucking lips.” He stared at the spreader bars keeping Dean’s legs apart and up to the slick hole he’d already fucked with a toy only moments ago.

Slowly Castiel picked up the paddle, one with holes so he could get the kind of swing he wanted, before pulling back and bringing it down on Dean’s ass hard.

The sound echoed in the room and combined with the shout that tore itself from Dean’s mouth.

Castiel closed his eyes to briefly savor it and grinning he started bringing the paddle down on Dean’s ass to pull the most beautiful moans and cries he’d heard in a long time. The ass presented to him was steadily getting redder until the prostitute was near sobbing at the burning pain racing through his ass.

“Fuck…look at that ass of yours.” Castiel reached out and touched one burning hot cheek, pressing against it, until it earned him a whimper Dean didn’t bother holding back. His thighs were trembling and his body shaking. It was merciful that Castiel had secured him so he was braced with his ass up or Dean might have faltered in his position.

Dean gasped, clenching his eyes shut, as lube slick fingers circled his rim before pressing inside and tugging on it. They moved a few more times in such a way before pressing inside and crooking to immediately zero in on his prostate.

His client stroked at it as he moaned and gasped, shoving his hips back into those fingers, until Castiel was pressing three inside and stretched him wide again. It burned and pulled a whimper out.

“I can see why you decided to become a whore.” The voice was rough, breath hot against his ear. “With an ass made for cock and lips to match.” Dean moaned as Castiel pressed his cock inside, thrusting hard, until he was buried balls deep.

Nails dug into Dean’s hips as the blue eyed man started thrusting hard into him, the harsh slap of skin against skin filled the room, as Dean moaned at the sensation. He’d been opened just enough that the burn was there but it wasn’t causing unbearable pain like some clients wanted. Instead the one fucking into him was going at a brutal pace, occasionally angling to drag over his prostate, as moans and gasps fell from his lips easily.

The pain in his ass from being spanked had him whimpering each time hips smacked against his burning cheeks.

He knew he would be feeling this one when the weekend was up. Dean had seen the toys that Mr. Novak had brought along and from how they had started off, with so many toys and the cockcage he still wore, it was more than obvious Castiel was going to get his money’s worth.

Warmth came closer along with a weight pressing him down before teeth nipped at his skin, biting just shy of drawing blood, while Castiel rutted against him. There were grunts and pleasured groans being puffed out against his skin as Dean tried to shift his legs but he was thoroughly secured down.

Castiel had made sure he had positioned Dean in such a way that he would be completely accessible for him, ass raised and head angled out should he choose to use Dean’s mouth.

“My pretty little whore. Love taking cock, don’t you? Want nothing more than to be fucked over and over until you’re sloppy with it, begging for more and hoarse from crying.” The words mixed with the moans and the high whine that escaped when Castiel brought his hand down on Dean’s thigh.

The slap seemed to resonate through him, moving up to send hot flares of pain from his abused ass, all the while Castiel kept thrusting forward and ignoring the hard cock Dean was suffering with. His cock remained caged, untouched and aching, with the metal locked around him.

He could feel when Castiel’s thrusts became wild, falling off their quick rhythm, before the man was slamming inside him and coming apart with a snarl. His breath hot against Dean’s back and all Dean could do was whimper at the feeling.

The prostitute felt the soft cock slip from his ass as Castiel moved around to remove the spreader bar and to unhook him. When his client was finished he hauled Dean up and dragged him towards the bed where there are several other toys. His arms were secured before Castiel tied his legs so they were spread, his body bent, with the bindings for them secured to the headboard as well.

It wasn’t the most comfortable position and he felt completely exposed as come leaked from his puffy hole but Castiel was getting one of the larger dildos. This one had a vibrating feature and Dean whimpered at the sight as it was slicked up before Castiel was nudging it against his hole.

There was no mistaking that this one would  _burn_  stretching him wide but he’d taken three cocks before and he could take every toy Castiel threw at him for the remainder of the weekend. It popped past the first ring of muscles as Castiel pushed it inside and watched greedily as Dean’s ass took every inch of the toy.

It burned more than he’d thought, being far wider and longer than Castiel’s cock, as it continued to push inside him.

“Made for fucking.” The words were murmured as Castiel turned the toy on before starting to thrust it inside Dean as he twisted in his bindings. Moans and soon desperate screams bounced off the wall as Dean felt a hand teasing his balls, moving up to his neglected cock.

It was a fine line between pain and pleasure as Castiel kept going until Dean was sobbing with need, begging for release, while Castiel recovered from his orgasm. Dean couldn’t focus on anything other than the blinding need and teasing pleasure as Castiel manipulated his body before the toy was moving away.

Blurred green eyes glanced at the man smirking at him, cheeks flushed and dark hair messy, as he guided his cock inside Dean and a whimper escaped. “That’s it, whore. Beg for it. Beg me to fuck your slutty hole until you’re slick with my come again.”

“Please please fuck me! I need it please.” His mouth worked as he watched those eyes go dark and that full mouth parted in pleasure. “Fuck me sloppy please! Please Mr. Novak. I need it!”

“That’s right. Tell me whose whore you are.”

“Yours! I’m your whore. Please fuck me, Mr. Novak.” His tongue darted out to wet his lips as Castiel bared his teeth and thrust in Dean’s ass once he’d moved himself close.

It was hard and rough, just like before, as Dean heard the headboard hitting against the wall with the force behind the thrusts. Sound was ripped from Dean, his throat scratchy with it, as Castiel kept snapping his hips forward to bury himself repeatedly inside Dean.

“There are so many things I’m going to do to your tight little body this weekend.” Castiel promised as he locked eyes with Dean’s, taking in the flush and the way sound spilled from those lips.

Dean’s ass clenched at the thought of what laid ahead for him. He was sure he’d need a day or two to recover before agreeing to another client with rougher needs.


End file.
